Upcoming Live Music Events

"Cinco de Mayo" Street Party and Celebration - Promenade at Sunset Walk

 Promenade at Sunset Walk 5 May 2026
ENTERTAINMENT FREE

Taste of Kissimmee

Kissimmee Lakefront Park 8 May 2026
MUSIC

iRISE EXPO 2026

 1901 Chief Osceola Trail 18 Jul 2026
BUSINESS FREE

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Upcoming Festivals Events

2026 Caribbean Fusion Festival | Caribbean And Floridian Association, Inc

 Kissimmee Lakefront Park 26 Apr 2026
FESTIVALS FREE

Osceola Pride

 1875 Silver Spur Ln, Kissimmee, FL 34744-6105, United States 28 Jun 2026
NONPROFIT

Silver Spurs Rodeo at Silver Spurs Arena at Osceola Heritage Park

 Silver Spurs Arena at Osceola Heritage Park 5 Jun 2026
TRIPS-ADVENTURES

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Upcoming Comedy Events

Francisco Ramos+Kelvin Pérez+Hombre Promedio - Comedia en Español

 3295 Oxford Dr 25 Jul 2026
USD 39

Gonzalo Mihail - NO TAN EN SERIO.

 3295 Oxford Dr 21 May 2026
COMEDY USD 29

Kel Pérez - Crowd Work Therapy.

 3295 Oxford Dr 21 Mar 2026
ENTERTAINMENT USD 29

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Trending Events in Kissimmee

“SPIN THE BLOCK” FASHION SHOW

 Alpha Tires&Wheels 3 May 2026
FASHION USD 31 TO 59

ILAN All Inclusive 2026

 Island Grove Winery 23 May 2026
FOOD-DRINKS USD 140

Promenade at Sunset Walk "Memorial 4 Day Weekend" May 22nd - May 25th

 Promenade at Sunset Walk 22 May 2026
CAR-SHOWS FREE

Speed Dating Event Tricks: Guide for Kissimmee Singles

 Kissimmee 4 Jun 2025
WORKSHOPS USD 23 TO 35

Osceola County High School Graduations

 1875 Silver Spur Ln, Kissimmee, FL, United States, Florida 34744 19 May 2026

Hot Wheels Monster Trucks Live Glow-N-Fire at Silver Spurs Arena at Osceola Heritage Park

 Silver Spurs Arena at Osceola Heritage Park 2 May 2026
MONSTER-TRUCK-SHOWS

Hot Wheels Monster Trucks Live Glow-N-Fire

 Osceola Heritage Park 3 May 2026
MONSTER-TRUCK-SHOWS

Hot Wheels Monster Trucks Live Glow-N-Fire

 Silver Spurs Arena at Osceola Heritage Park 2 May 2026
MONSTER-TRUCK-SHOWS

157th Silver Spurs Rodeo

 1875 Silver Spur Ln, Kissimmee, FL, United States, Florida 34744 5 Jun 2026
RODEO

Alex Campos y Ingrid Rosario: Unidos en Alabanza

 Silver Spurs Arena At OHP 30 May 2026

Silver Spurs Rodeo

 Osceola Heritage Park/Silver Spurs Arena 6 Jun 2026
RODEO

Lip Sync Battle

 1901 Chief Osceola Trl, Kissimmee, FL 34744-6112, United States 25 Apr 2026
ART

Silver Spurs Rodeo

 Silver Spurs Arena @ Osceola Heritage Park 5 Jun 2026
RODEO

Alex Manga, Enaldo Barrera Jr. in Kissimmee

 Fonda Dulce Jesus Mio 22 May 2026

Alex Campos

 Silver Spurs Arena at Osceola Heritage Park 30 May 2026

More things to do in Kissimmee

Live Music
Festivals
Comedy
Speed Dating
Music Festivals
St. Patrick's Day
Carnivals
Food Truck Festivals
Pop-Ups